Predicting rate constants of hydroxyl radical reactions with organic pollutants: Algorithm, validation, applicability domain, and mechanistic interpretation

Atmospheric Environment

Volumn 43, Issue 5, 2009, Pages 1131-1135

  Wang, Ya nan ^a   Chen, Jingwen ^a   Li, Xuehua ^a   Wang, Bin ^a   Cai, Xiyun ^a   Huang, Liping ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Hydroxyl radical; PLS; QSAR; Rate constant

Indexed keywords

DO-MAINS; EXPERIMENTAL DATUMS; EXTERNAL VALIDATIONS; HALOGEN ATOMS; HYDROXYL RADICAL; HYDROXYL RADICAL REACTIONS; MECHANISTIC INTERPRETATIONS; MOLECULAR ABILITIES; OH REACTIONS; PARTIAL LEAST SQUARES; PLS; PREDICTIVE CAPABILITIES; PREDICTIVITY; QSAR; QUANTITATIVE STRUCTURES; REMOVAL PROCESSES; SI ATOMS; STRUCTURAL DESCRIPTORS; STRUCTURAL FACTORS; WILLIAMS;

ATOMIC PHYSICS; ATOMS; BIOCHEMISTRY; BROMINE COMPOUNDS; CHLORINE COMPOUNDS; CRYSTAL ATOMIC STRUCTURE; CURVE FITTING; FUNCTIONAL GROUPS; ORGANIC CHEMICALS; ORGANIC COMPOUNDS; ORGANIC POLLUTANTS; REACTION KINETICS; REACTION RATES; SEMICONDUCTING SILICON COMPOUNDS; SULFUR COMPOUNDS;

RATE CONSTANTS;

ALGORITHM; ATMOSPHERIC POLLUTION; HALOGEN; HYDROXYL RADICAL; LEAST SQUARES METHOD; OECD; ORGANIC POLLUTANT; REACTION RATE; REMOVAL EXPERIMENT; TROPOSPHERE;

EID: 58249133819     PISSN: 13522310     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.atmosenv.2008.11.012     Document Type: Article

References (41)

1. Atkinson R. Kinetics and mechanisms of the gas-phase reactions of the hydroxyl radical with organic compounds under atmospheric conditions. Chemical Reviews 85 (1985) 69-201
2. Atkinson R. Gas-phase reactions of the hydroxyl radical. Chemical Reviews 86 (1986) 69-201
3. Atkinson R. A structure-activity relationship for the estimation of rate constants for the gas-phase reactions of OH radicals with organic compounds. International Journal of Chemical Kinetics 19 (1987) 799-828
4. Atkinson R. Estimation of gas-phase hydroxyl radical rate constants for organic chemicals. Environmental Toxicology and Chemistry 7 (1988) 435-442
5. Atkinson R. Kinetics and mechanisms of the gas-phase reactions of the hydroxyl radical with organic compounds. Journal of Physical and Chemical Reference Data Monographs 1 (1989) 1-216
6. Atkinson R. Gas-phase tropospheric chemistry of organic compounds. Journal of Physical and Chemical Reference Data Monographs 2 (1994) 1-246
7. Atkinson R. Kinetics of the gas-phase reactions of OH radicals with alkanes and cycloalkanes. Atmospheric Chemistry and Physics Discussions 3 (2003) 4183-4358
8. Chen J.W. Quantitative Structure-property Relationships and Quantitative Structure-activity Relationships of Organic Pollutants (1999), Dalian University of Technology Press, China
9. EPI Suite™ Available from: .
10. Eriksson L., Jaworska J., Worth A.P., Cronin M.T.D., McDowell R.M., and Gramatica P. Methods for reliability and uncertainty assessment and for applicability evaluations of classification and regression-based QSARs. Environmental Health Perspectives 111 (2003) 1361-1375
11. Golbraikh A., and Tropsha A. Beware of q2!. Journal of Molecular Graphics & Modelling 20 (2002) 269-276
12. Gramatica P. Principles of QSAR models validation: internal and external. QSAR & Combinatorial Science 26 (2007) 694-701
13. Gramatica P., Pilutti P., and Papa E. A tool for the assessment of VOC degradability by tropospheric oxidants starting from chemical structure. Atmospheric Environment 38 (2004) 6167-6175
14. Gramatica P., Pilutti P., and Papa E. Validated QSAR prediction of OH tropospheric degradation of VOCs: splitting into training-test sets and consensus modeling. Journal of Chemical Information and Computer Science 44 (2004) 1794-1802
15. Güsten H. Predicting the abiotic degradability of organic pollutants in the troposphere. Chemosphere 38 (1999) 1361-1370
16. Güsten H., Klasinc L., and Maric D. Prediction of the abiotic degradability of organic compounds in the troposphere. Journal of Atmospheric Chemistry 2 (1984) 83-93
17. Huang X.Y., Chen J.W., Gao L.N., Ding G.H., Zhao Y.Z., and Schramm K.-W. Data evaluations and quantitative predictive models for vapor pressures of polycyclic aromatic hydrocarbons at different temperatures. SAR and QSAR in Environmental Research 15 (2004) 115-125
18. Jaworska J.S., Nikolova J.N., and Aldenberg T. QSAR applicability domain estimation by projection of the training set in descriptor space: a review. ATLA-Alternatives to Laboratory Animals 33 (2005) 445-459
19. Karelson M., Lobanov V.S., and Katritzky A.R. Quantum-chemical descriptors in QSAR/QSPR studies. Chemical Reviews 96 (1996) 1027-1043
20. Klamt A. Estimation of gas-phase hydroxyl radical rate constants of organic compounds from molecular orbital calculations. Chemosphere 26 (1993) 1273-1289
21. Klamt A. Estimation of gas-phase hydroxyl radical rate constants of oxygenated compounds based on molecular orbital calculations. Chemosphere 32 (1996) 717-726
22. Klo{combining double acute accent}pffer W. Environmental hazard assessment of chemicals and products. Part VI. Abiotic degradation in the troposphere. Chemosphere 33 (1996) 1083-1099
23. Kolossov E., and Stanforth R. The quality of QSAR models: problems and solutions. SAR and QSAR in Environmental Research 18 (2007) 89-100
24. Kwok E.S.C., Aschmann S.M., and Atkinson R. Rate constants for the gas-phase reaction of selected carbamates and lactates. Environmental Science & Technology 30 (1996) 329-334
25. Kwok E.S.C., and Atkinson R. Estimation of hydroxyl radical reaction rate constants for gas-phase organic compounds using a structure-reactivity relationship: an update. Atmospheric Environment 29 (1995) 1685-1695
26. Long X.X., and Niu J.F. Estimation of gas-phase reaction rate constants of alkylnaphthalenes with chlorine, hydroxyl and nitrate radicals. Chemosphere 67 (2007) 2028-2034
27. Meylan W.M., and Howard P.H. A review of quantitative structure-activity relationship methods for the prediction of atmospheric oxidation of organic chemicals. Environmental Toxicology and Chemistry 22 (2003) 1724-1732
28. Netzeva T.I., Worth A.P., Aldenberg T., Benigni R., Cronin M.T.D., Gramatica P., Jaworska J.S., Kahn S., Klopman G., Marchant C.A., Myatt G., Nikolova-Jeliazkova N., Patlewicz G.Y., Perkins R., Roberts D.W., Schultz T.W., Stanton D.T., van de Sandt J.J.M., Tong W., Veith G., and Yang C. Current status of methods for defining the applicability domain of (Quantitative) Structure-Activity Relationships. The report and recommendations of ECVAM Workshop 52. Alternatives to Laboratory Animals 33 (2005) 155-173
29. Öberg T. A QSAR for the hydroxyl radical reaction rate constant: validation, domain of application, and prediction. Atmospheric Environment 39 (2005) 2189-2200
30. OECD. Guidance Document on the Validation of (Quantitative) Structure-Activity Relationships [(Q)SAR] Models (2007), Organisation for Economic Co-Operation and Development, Paris, France
31. Sabljic A., and Peijnenburg W. Modeling lifetime and degradability of organic compounds in air, soil, and water systems (IUPAC Technical Report). Pure and Applied Chemistry 73 (2001) 1331-1348
32. Schultz T.W., and Cronin M.T.D. Essential and desirable characteristics of ecotoxicity quantitative structure-activity relationships. Environmental Toxicology and Chemistry 22 (2003) 599-607
33. Stewart J.J.P. Optimization of parameters for semiempirical methods I. Method. Journal of Computational Chemistry 10 (1989) 209-220
34. Stewart J.J.P. Optimization of parameters for semiempirical methods II. Applications. Journal of Computational Chemistry 10 (1989) 221-264
35. Todeschini R., and Consonni V. Handbook of Molecular Descriptors (2000), Wiley-VCH, Weinheim, Germany
36. Tropsha A., Gramatica P., and Gombar V.K. The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models. QSAR & Combinatorial Science 22 (2003) 69-77
37. Tunkel J., Mayo K., Austin C., Hickerson A., and Howard P. Practical considerations on the use of predictive models for regulatory purposes. Environmental Science & Technology 39 (2005) 2188-2199
38. Westad F., and Martens H. Variable selection in near infrared spectroscopy based on significance testing in partial least squares regression. Journal of Near Infrared Spectroscopy 8 (2000) 117-124
39. Wold S., Sjo{combining double acute accent}stro{combining double acute accent}m M., and Eriksson L. PLS-regression: a basic tool of chemometrics. Chemometrics and Intelligent Laboratory Systems 58 (2001) 109-130
40. Yan C.L., Chen J.W., Huang L.P., Ding G.H., and Huang X.Y. Linear free energy relationships on rate constants for the gas-phase reactions of hydroxyl radicals with PAHs and PCDD/Fs. Chemosphere 61 (2005) 1523-1528
41. Yasri A., and Hartsough D. Toward an optimal procedure for variable selection and QSAR model building. Journal of Chemical Information and Computer Science 41 (2001) 1218-1227